Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/62—Oxygen or sulfur atoms
  • C07D213/63—One oxygen atom
  • C07D213/64—One oxygen atom attached in position 2 or 6
  • C07D213/643—2-Phenoxypyridines; Derivatives thereof

Definitions

• This invention relates to a process for the preparation of derivatives of propenoic acid which are useful as fungicides or as chemical intermediates in the preparation of fungicides.
• a process for the preparation of a compound of general formula (I): ##STR1## wherein the aromatic rings M and P optionally carry one or more substituents which are not reactive under the conditions of the process which comprises reacting a compound of general formula (II): ##STR2## wherein X is halogen (preferably iodine, chlorine or bromine) or other good leaving group with a phenol of general formula (III): ##STR3## in the presence of a base, or with a salt of the phenol (III), preferably in the presence of a catalyst which comprises a suitable transition metal or transition metal salt or compound or a mixture thereof.
• compounds of general formula (I) can be obtained by reaction of compounds (II) with salts derived from phenols of general formula (III) by prior treatment of the phenols with base.
• the additional presence of a base during the coupling reaction is not required.
• compound (II) other good leaving groups which X may be include C 1-4 alkylsulphonyl, optionally substituted aryl(suitably phenyl)sulphonyl and nitro.
• a solvent may be employed in carrying out the process of the invention.
• Suitable solvents are those in which both compounds (II) and (III) (or salts derived therefrom) are soluble or partially soluble and which do not react with either of these substrates under the condition of the reaction.
• Solvents which may be used include dipolar aprotic solvents such as N,N-dimethylformamide, dimethylsulphoxide, N,N-dimethylacetamide and methylisobutylketone. In certain cases, when either of the substrates is a liquid under the conditions of the reaction, it is possible to perform the reaction in the absence of an added solvent.
• Suitable bases for use in the process are those which act either by abstraction of the phenolic proton of compound (III) prior to reaction with substrate (II) or by neutralisation of any acid produced during the reaction, without reacting significantly with substrate (II) or product (I).
• An example of such a base is anhydrous potassium carbonate.
• Suitable transition metals or transition metal salts or compounds which may catalyse the process include copper metal, copper salts and compounds and nickel salts and compounds, such as copper bronze and copper (I) chloride, which may be used separately or in admixture (see, for example, A. A. Moroz and M. S. Shvartsberg, Russian Chemial Reviews, 1974, 43 (8), 679-689).
• the process may be conducted over a wide range of temperatures.
• the temperature will be chosen so that reaction occurs at a reasonable and convenient rate. This will usually be in the range 100° C. to 200° C. depending on the reactivity of the substrates (II) and (III) and the nature of the catalyst.
• the compound (II) is treated with a phenol in the presence of potassium carbonate in N,N-dimethylformamide at about 150° C.
• the product is isolated by extraction into ether followed by evaporation and recrystallisation (from a suitable solvent or solvent mixture).
• the product may be purified by chromatography.
• the process of the invention is of special interest in the preparation of fungicidal compounds; for instance, those described in EP-A-0243012 and, in particular, those
• A, B, D and Y which may be the same or different, are hydrogen or halogen atoms, or optionally substituted alkyl, optionally substituted alkenyl, optionally substituted aryl, optionally substituted heteroaryl, optionally substituted alkynyl, optionally substituted alkoxy, optionally substituted aryloxy, optionally substituted heteroaryloxy, optionally substituted arylalkoxy, optionally substituted acyloxy, optionally substituted sulphonyloxy, optionally substituted amino, optionally substituted arylazo, acylamino, nitro, cyano, --CO 2 R 1 , --CONR 2 R 3 , --COR 4 , --CR 5 ⁇ NR 6 , or --N ⁇ CR 7 R 8 groups, or the groups A and B, when they are in adjacent positions on the phenyl ring, may join to form a fused ring, optionally containing one or more heteroatoms;
• the process may also be used to prepare chemical intermediates useful in the preparation of fungicides.
• the substrate of general formula (II) may be prepared according to processes outlined in EP-A-0243012.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Pyridine Compounds (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Hydrogenated Pyridines (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

Applications Claiming Priority (2)

Publications (1)

Family

ID=10625392

Family Applications (1)

Country Status (7)

Families Citing this family (7)

Citations (12)

• 1987
  • 1987-10-15 GB GB878724251A patent/GB8724251D0/en active Pending
• 1988
  • 1988-09-28 EP EP88308963A patent/EP0312221B1/en not_active Expired
  • 1988-09-28 ES ES88308963T patent/ES2052737T3/es not_active Expired - Lifetime
  • 1988-09-28 DE DE8888308963T patent/DE3875447T2/de not_active Expired - Fee Related
  • 1988-10-13 JP JP25608688A patent/JP2771994B2/ja not_active Expired - Lifetime
  • 1988-10-14 DK DK574688A patent/DK170858B1/da not_active IP Right Cessation
  • 1988-10-17 US US07/258,661 patent/US5039810A/en not_active Expired - Fee Related

Patent Citations (12)

Non-Patent Citations (7)

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